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Sorafenib
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Name

Sorafenib

 EINECS 608-209-4
CAS No. 284461-73-0 Density 1.454 g/cm3
PSA 92.35000 LogP 6.08660
Solubility 100μg/L at 20℃ Melting Point 202-204 °C
Formula C21H16ClF3N4O3 Boiling Point 523.3 °C at 760 mmHg
Molecular Weight 464.831 Flash Point 270.3 °C
Transport Information N/A Appearance light yellow solid
Safety 36-37-39 Risk Codes 68/20/21/22-37/38
Molecular Structure Molecular Structure of 284461-73-0 (Sorafenib tosylate) Hazard Symbols Xi
Synonyms

BAY43-9006;N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-[4-[2-(N-methylcarbamoyl)-4-pyridyloxy]phenyl]urea;

Article Data 59

Sorafenib Synthetic route

343247-69-8

4-chloro-3-trifluoromethylphenylurea

1154243-75-0

[4-(4-bromophenoxy)(2-pyridyl)]-N-methylcarboxamide

284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: [4-(4-bromophenoxy)(2-pyridyl)]-N-methylcarboxamide With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 20℃; for 0.5h;
Stage #2: 4-chloro-3-trifluoromethylphenylurea In 1,4-dioxane at 80 - 100℃; for 1h; Solvent; Reagent/catalyst;		97.9%
With t-BuBrettPhos; palladium diacetate; caesium carbonate In tetrahydrofuran; water at 75℃; for 5h; Inert atmosphere;206 mg
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

(4-chloro-3-trifluoromethyl aniline)carboxylic acid allyl ester

284461-73-0

sorafenib

Conditions
ConditionsYield
With 1-Methylpyrrolidine In dichloromethane at 30℃; for 24h; Solvent; Temperature;97.6%
1129683-83-5

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

1209459-88-0

4-bromo-pyridine-2-carboxylic acid methyl amide

284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 50 - 60℃; for 0.5h;
Stage #2: 4-bromo-pyridine-2-carboxylic acid methyl amide In 1-methyl-pyrrolidin-2-one for 2h; Reagent/catalyst; Reflux;		96.7%
611226-36-9, 1061231-84-2

4-hydroxy-N-methylpyridine-2-carboxamide

1129683-83-5

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

284461-73-0

sorafenib

Conditions
ConditionsYield
at 132℃;96.3%
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

284461-73-0

sorafenib

Conditions
ConditionsYield
With zirconia grinding balls In acetonitrile for 4h; Milling;96%
In ethyl acetate at 20 - 30℃; Large scale;94.2%
In dichloromethane93%
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1187086-96-9

N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

284461-73-0

sorafenib

Conditions
ConditionsYield
In chlorobenzene at 70 - 75℃; for 0.25h; Product distribution / selectivity;95%
In ethyl acetate at 20 - 50℃; for 2.75h;77%
With potassium carbonate In dichloromethane for 8h; Milling;72%
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

1737-36-6

4-chloro-3-(trifluoromethyl)benzoic acid

2,2,2,-trichloroethoxycarbonyl azide

284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid; 2,2,2,-trichloroethoxycarbonyl azide With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Curtius Rearrangement; Inert atmosphere;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;		93%
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

320-51-4

4-chloro-3-trifluoromethyl-aniline

530-62-1

1,1'-carbonyldiimidazole

284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 16h; Inert atmosphere;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane Inert atmosphere;		91%
Stage #1: 4-chloro-3-trifluoromethyl-aniline; 1,1'-carbonyldiimidazole In dichloromethane at 25 - 35℃; for 18h;
Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane at 25 - 35℃; for 48.75h;		90 g
123-30-8

4-amino-phenol

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

220000-87-3

4-chloro-N-methylpicolinamide

284461-73-0

sorafenib

Conditions
ConditionsYield
Stage #1: 4-amino-phenol; 4-chloro-3-(trifluoromethyl)phenyl isocyanate; 4-chloro-N-methylpicolinamide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 80℃; Solvent; Reagent/catalyst; Temperature;		90.6%
1129683-83-5

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

220000-87-3

4-chloro-N-methylpicolinamide

284461-73-0

sorafenib

Conditions
ConditionsYield
With potassium carbonate In toluene Heating;90%
With tetrabutylammomium bromide; potassium iodide; potassium hydroxide In tetrahydrofuran at 80℃; for 10h; Solvent; Reagent/catalyst;89.4%
Stage #1: 4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol With potassium tert-butylate In N,N-dimethyl-formamide for 2h;
Stage #2: 4-chloro-N-methylpicolinamide With potassium carbonate at 80℃; for 6h;		50%

Sorafenib Chemical Properties

Sorafenib is a drug approved for the treatment of primary kidney cancer , also for the treatment of advanced renal cell carcinoma, and advanced primary liver cancer (hepatocellular carcinoma).It's usually light yellow solid.

Molecular Formula:  C21H16ClF3N4O3
Molecular Weight:  464.83
Melting point:  202-204°C

Sorafenib Uses

Sorafenib is a potent RAF kinase inhibitor,and it is used an antineoplastic agent.

Sorafenib Safety Profile

Side effects:skin rash, hand-foot skin reactions, diarrhea, and hypertension. It has also been implicated in the development of reversible posterior leukoencephalopathy syndrome.
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